When U.S. District Court Judge Garr King announced in November he would step down this spring from working full time, the move puzzled some observers.

A Democrat appointed in 1997 by President Clinton, King will be departing during the final year of the Bush administration. And that's curious, because it opens the door for a more conservative replacement on Portland's federal bench before a Democrat may be taking over the White House and has a chance to make the appointment.

Now an election-year political storm may be brewing over who should replace King, 71. Through interviews with highly placed lawyers and political insiders, WW has learned that the favored candidate is U.S. Attorney Karin Immergut, Oregon's top federal prosecutor.

Eight sources—many of whom declined to speak on the record—said Immergut is the favorite of U.S. Sen. Gordon Smith, who as Oregon's Republican senator will make the key recommendation to the Republican White House on whom to nominate.

"What I've heard is that it's going to be Karin Immergut; there's going to be no question about it," says a Portland lawyer with extensive political connections. Steven Sherlag, a lawyer who works extensively in federal court, agrees. "I'd be surprised if it didn't happen," Sherlag says.

(Tempted to stop reading because you think federal judges don't affect you? Think of Dec. 28, when U.S. District Court Judge Michael Mosman, a Bush appointee, delayed implementing same-sex domestic partnerships in Oregon because of a legal challenge. Mosman faced questions during his 2003 confirmation over a memo he wrote in 1986 that was viewed as hostile to gay rights. See "State of Disunion," WW , Jan. 9, 2008, for more.)

Immergut's status as a moderate, pro-choice Republican might seem to make her a safe choice for Smith as he faces a tough 2008 re-election bid in Democratic-leaning Oregon. By all accounts, Immergut is a highly competent prosecutor who's widely admired in the legal community. "She has a reputation as a very good lawyer without any ideological bent," says Michael Williams, a high-profile Portland trial lawyer.

But in today's charged political climate, Immergut could face stiff opposition from U.S. Sen. Ron Wyden (D-Ore.) and powerful members of Congress because of several pieces of baggage she brings—including work she did 10 years ago as a team member on Special Prosecutor Ken Starr's investigation of President Clinton's sexual foibles.

Immergut confirmed to WW that she was among the 19 candidates who applied for the King judicial seat, one of eight full-time slots on the federal bench in Portland. Otherwise she declined to comment, except to praise King and say that his replacement has "large shoes to fill." Smith's office, which will recommend a nominee to the White House in the coming weeks, declined to comment on Immergut or to turn over a list of the final eight candidates. Instead, they referred questions to a six-member committee of local lawyers that will interview the finalists on Jan. 22.

"There's no done deal, and I don't feel like I should tell you who the list of interviewees are," says former Republican state senator Neil Bryant, Smith's choice to chair the selection committee. "But no one has been selected at this point and the committee has expressed no preference toward any one candidate."

The federal bench is a plum post, with a $165,000 salary and lifetime job security. Despite the fact that Immergut—who is 47 and now makes $149,000 a year with no job security—is clearly qualified, insiders say there are several factors that could hold up her appointment, the foremost being her work for Starr.

It was Immergut who personally questioned Monica Lewinsky in an Aug. 6, 1998, deposition, famously asking whether the president was wearing pants when he received oral sex. Now, with Sen. Hillary Clinton (D-N.Y.) a leading presidential candidate and Clinton's friend Sen. Charles Schumer (D-N.Y.) on the Senate Judiciary Committee, Immergut's appointment could get a rough reception in Congress.

Immergut, who was a Multnomah County deputy district attorney when she went to work for Starr, has called the job a young prosecutor's dream. But it was one that came with a political price. A longtime Democrat, Immergut registered as nonpartisan shortly before going to work for Starr. After Bush took the White House, she registered as a Republican in December 2001—the same month that Mosman, the U.S attorney in Portland at the time, hired her on as a federal prosecutor.

When Mosman became a federal judge in 2003, Immergut replaced him as top prosecutor. As U.S. attorney in charge of a 107-person office, she managed to buoy her staff's morale even under the train-wreck reign of former U.S. Attorney General Alberto Gonzales, who was accused by Democrats of firing nine U.S. attorneys for their insufficient loyalty to the Bush administration.

Rightly or wrongly, sources say Immergut also could face skepticism by the public and Congress for keeping her job when others were purged. And she'll face questioning over her role in the embarrassing case against Brandon Mayfield, a Portland lawyer falsely linked to the 2004 Madrid train bombings.

Mayfield says Immergut shouldn't get the job because of her role in his case.

"It was botched at all levels," he told WW . "I would hold her more responsible than anybody at a local level."

Because they're normally conducted out of public view, fights over judicial appointments can turn into nasty political brawls. The president officially nominates judicial candidates, but it's the state's senior senator from the party that holds the White House who makes the decisive recommendation. Conflict arises when there's pressure in Congress to block a nominee, usually when a troubled bit of their history comes up during Senate confirmation.

That's not supposed to happen with Oregon, where Wyden and Smith have a gentlemen's agreement to avoid public spats by recommending only nominees they can both support. When Clinton was in the White House, Smith went along with Wyden's two judicial picks, and Wyden signed off when Smith picked Mosman under Bush.

But if Smith stays with Immergut as his prime pick, it's still an open question whether Wyden will go along. Wyden's chief of staff, Josh Kardon, says it's too early to say.

Timing is critical for Smith because of a tradition in Congress that in the final year of a president's term, judicial appointments gradually stop moving through Congress until a new president is in office. If Smith wants Bush to appoint King's replacement, he has a very small window of time and probably only one chance to pick someone Wyden and Congress can accept. If Smith's nominee fails, it will be the next president who fills the seat.

For Immergut, too, timing is crucial. If a Democrat takes the White House, she would likely lose her job as U.S. attorney and would certainly be at the back of the line for judicial nominations. And if it's President Hillary Clinton, as one lawyer puts it, unless Immergut is on the federal bench in 2009, "Karin Immergut is done under Clinton."

FACT:

Jan. 17 marks the 10-year anniversary of the day the Lewinsky scandal broke on the Internet.